Hydrochloric Acid → Methyl 4-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)butanoic Acid Methyl Ester

HRID 2388658Notes

Reaction equation

HRID 2388658 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:15])[CH:5]([CH3:14])[CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][NH:9]1.C(N(CC)CC)C.[CH3:23][O:24][C:25]1[CH:30]=[C:29]([CH3:31])[C:28]([S:32](Cl)(=[O:34])=[O:33])=[C:27]([CH3:36])[CH:26]=1.Cl>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:15])[CH:5]([CH3:14])[CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][N:9]1[S:32]([C:28]1[C:29]([CH3:31])=[CH:30][C:25]([O:24][CH3:23])=[CH:26][C:27]=1[CH3:36])(=[O:34])=[O:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 159174964-Methoxy-2,6-dimethylbenzene-1-sulfonyl chlorideHCID 67316706Methyl 4-(piperidin-2-yl)butanoic acid methyl ester hydrochloride

Product 1

HCID 67316484Methyl 4-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)piperidin-2-yl)butanoic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Methyl 4-(piperidin-2-yl)butanoic acid methyl ester hydrochloride (1.26 g, 5.683 mmol) was dissolved in methylene chloride (25 ml) and triethylamine (4 ml, 28.417 mmol) and a solution of 4-methoxy-2,6-dimethylbenzenesulfonic acid chloride (2.67 g, 11.37 mmol) [see AC5, stage 1) in methylene chloride (10 ml) was added. The mixture was stirred at room temperature overnight. 1 mol/l HCl solution (10 ml) was added to the reaction mixture, phase separation, extraction of the aqueous phase with methylene chloride (2×20 ml). The combined organic phases were washed with sat. sodium chloride solution (20 ml), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with hexane/methylene chloride/ether (400/100/50). The yield was 1.65 g (75%).

Workup

  1. additionwas added
  2. washThe combined organic phases were washed with sat. sodium chloride solution (20 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography (silica gel) with hexane/methylene chloride/ether (400/100/50)

Sources & evidence

ORD record
ord-9d8123e5b9e44ff3868408747bf50f03
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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